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For the given reaction \[(B)\xleftarrow{NaB{{H}_{4}}}PhCH=CH-CHO\xrightarrow[2){{H}_{3}}{{O}^{+}}]{1)LAH,ether}(A)\]
The products (A) and (B) are:
(A) 168飞艇 f5922c25f27f4b0a83a7e611506ea32f
(B) 168飞艇 72fe4a1ab14f48c8086d7d310dd676b9
(C) 168飞艇 7e13d346dbe7fb30eb25515310bf65e3
(D) 168飞艇 7e2d0d3353ff8c0e9f0d2396be30dd2e

Answer
VerifiedVerified
300.6k+ views
Hint: LAH stands for Lithium Aluminium Hydride and $NaB{{H}_{4}}$ is sodium borohydride. Both lithium aluminium hydride and sodium hydride are reducing agents but LAH is more stronger.

Complete step by step solution:
- It is known that Lithium Aluminium Hydride (LAH) is a strong, unselective reducing agent for polar double bonds and is a source of hydride ions.
- LAH will reduce aldehydes, ketones, esters, carboxylic acid chlorides, carboxylic acids and even carboxylate salts to alcohols. Also, it reduces amides and nitriles to amines.
- Sodium borohydride is also used as a reducing agent in organic chemistry. It is commonly used to reduce ketones by donating hydride ions. This compound can be used in aqueous solution because it is not that reactive compared to LAH.
- Now, coming to the question, the compound which is reacted with both sodium borohydride and LAH is 3-Phenylprop-2-enal and its common name is cinnamaldehyde.
- We know that alkene gives electrophilic addition reaction so it will not react with sodium borohydride so sodium borohydride will only reduce the carbonyl group into corresponding alcohol. The reaction can be given as under.
168飞艇 19536a67ace94f1bc60c586ce1b37fb4
But since, the given compound is alpha-beta unsaturated aldehyde so there is conjugation between alkene and carbonyl, so with LAH carbonyl and alkenes also get reduced. That means we will get an alkene functional group converted into alkane as well.
168飞艇 7981a2f1c367f4f2a621d8ba1656c323

Therefore, from above we can conclude that option (D) is the correct option to the given question.

Note:
It should be remembered that in order to reduce aldehyde or ketone selectively without reducing carbon-carbon double bond in the same molecule, a reducing agent hydroborane known as 9-BBN is also used. Also, you should remember that catalytic hydrogenation can reduce both the double bond and carbonyl group simultaneously.